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SoldSingle Family ResidenceSold

5058 Windward Avenue

Sarasota, FL 34242

$3,250,000

  • 3Beds
  • 3Baths3 full
  • 3,471Sq Ft
  • $936Per Sq Ft
  • 0.33Acres
  • 2019Built
Subdivision
Sara Sands
County
Sarasota
MLS®
A4667422

Overview

This custom-built home received the “Best Overall” award in the 2021 Manatee and Sarasota County Parade of Homes. Experience the pinnacle of Siesta Key waterfront living in this 2019-built masterpiece by Nutter Custom Construction. Designed with precision and built to last, this solar-powered coastal retreat sits on high elevation and spans over 3,400 living square feet, offering 3 bedrooms, 3 baths, and two versatile flex rooms that redefine modern island living. Every element blends elegance, performance, and peace of mind. You walk into a wide-open floor plan that immediately draws you in. To the left, the primary suite offers total privacy with a spacious bedroom, spa-inspired bathroom featuring double vanities, a soaking tub, glass-enclosed shower with 4 shower heads, and a private outdoor shower with 2 shower heads, connected directly to the master bath a truly open-air sanctuary. To the right, your dedicated office provides focus and functionality and can easily serve as a fourth bedroom, with the flex room ideal for a home office or bonus space. The heart of the home opens to expansive living and dining spaces with a chef’s kitchen showcasing high-end cabinetry, premium flooring, designer lighting, and top-of-the-line Sub-Zero and Wolf appliances. Each guest bedroom includes its own private en-suite bath, offering comfort and privacy for family and visitors alike. A large walk-in pantry and laundry room are conveniently positioned near the kitchen. A whole-home water softening system, an In-wall pest control system with access ports, 2 air conditioning systems to keep the home evenly comfortable during the warmest weather, and 2 tankless water heaters to provide plenty of hot water. An oversized three-car garage for everyday ease. An additional flex room opens to the pool through oversized sliders, perfect for a second office, game room, or guest suite. There are automated window shades in the living room and game room. The home runs entirely on solar power and includes a multi-room sound system that fills the home and outdoor living space with your favorite music. Massive hurricane-rated sliding glass doors wrap the back of the home, creating a seamless flow to your backyard oasis, including landscape lighting and an irrigation system. An Integrated Security System with perimeter cameras provides extra peace of mind. Step out onto the beautiful travertine pool deck, featuring a heated pool and champagne-edged spa, outdoor lounge, and covered dining area with a built-in outdoor chef’s kitchen powered by propane, perfect for entertaining in style, and all with a sunset view. Beyond the pool, enjoy a lush, manicured backyard with direct access to the wide Siesta Key Grand Canal. A dedicated 14,000-pound boat lift allows you to launch your boat with ease, making days on the water effortless. A separate private docking area is available for your friends to arrive by boat or for jet skis. Enjoy kayaking, paddleboarding, and scenic canal rides, or simply relax and take in the sunsets from your extended concrete pad with a built-in concrete firepit, ideal for gatherings by the water. Every detail of this home is custom-crafted, from its hurricane-rated construction and elevated-lot placement to its energy-efficient systems and timeless coastal design. 5058 Windward Ave isn’t just a home, it’s a statement in waterfront living: high elevation, solar-powered, elegant, and built for those who expect the very best on Siesta Key.

Listing Snapshot

Price
$3,250,000
Days On Site
N/A
Bedrooms
3
Inside Area (SqFt)
3,471 sqft
Total Baths
3
Full Baths
3
Partial Baths
0
Lot Size
0.33 Acres
Year Built
2019
MLS® Number
A4667422
Status
Sold
Property Tax
$28,719.17 (2025)
HOA/Condo/Coop Fees
N/A
Sq Ft Source
Builder

Property Details

General Features

18 items
Acres
0.33
Attached Garage
Yes
Direction Faces
East
Foundation
Slab
Garage
Yes
Garage Spaces
3
Green Energy Efficient
Appliances
Levels
One
Parking
Driveway, Garage Door Opener, Attached
Pets
Yes
Property Sub Type
Single Family Residence
Security
Security System, Smoke Detector(s)
Sewer
Public Sewer
SqFt Total
4,800
Style
Key West
Utilities
Cable Available, Electricity Available, Sewer Available, Water Available
Water Source
Public
Zoning
RSF2

Interior Features

16 items
Appliances
Cooktop, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Cooling
Central Air, Zoned
Flooring
Hardwood, Tile
Furnished
Unfurnished
Heating
Heat Pump
Interior
Built-in Features, Cathedral Ceiling(s), Crown Molding, Eat-in Kitchen, High Ceilings, Open Floorplan, Walk-In Closet(s)
Laundry Features
Laundry Room
Spa
Yes

Rooms

RoomDimensionsLevelFeatures
Bedroom 212x14FirstCeiling Fan(s)
Bedroom 312x14FirstCeiling Fan(s)
Dining Room18x14First
Game Room14x17First
Kitchen19x14FirstKitchen Island
Living Room26x19First
Master Bedroom15x22First
Office12x15.5First

Exterior Features

14 items
Construction Details
Block, Concrete, Stucco
Exterior
Outdoor Kitchen, Dock
Lot Features
Level, Paved, Waterfront
Other Structures
Outdoor Kitchen
Patio And Porch
Front Porch
Pool Features
Gunite, In Ground, Tile, Private
Private Pool
Yes
Roof
Metal
Spa
Yes
Spa Features
In Ground
View
Canal, Water
Waterfront
Yes
Waterfront Features
Canal Front
Waterview
Canal, Water

Community Features

4 items
MLS Area
34242 - Sarasota/Crescent Beach/Siesta Key
Township
37
Financing Terms Available
Cash, Conventional, FHA, VA Loan
Roads
Asphalt

Location

5058 Windward Avenue, Sarasota, FL 34242 · 34242 - Sarasota/Crescent Beach/Siesta Key

$17M$15M$12M
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Neighborhood & Commute

ZIP Code 34242

Median household income
$117,603
Income per person
$109,238
Households
4,295
Average household size
1.88
Median age
66.2

Source: Walk Score.

Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.

Schools

Elementary School
Phillippi Shores Elementary
Middle School
Brookside Middle
High School
Sarasota High

Price & Status History

  1. Listing updated with changes from the MLS®
  2. Status changed to Closed
  3. Price changed to $3,500,000

Friends & Family

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Listing courtesy of KELLER WILLIAMS ON THE WATER S (941) 929-3183

Stellar MLS

Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.

Last checked: 2026-11-11 01:08 AM EST

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